Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds

被引：29
作者：
Padmanaban, Sudakar [1 ,2 ]
Gunasekar, Gunniya Hariyanandam [3 ]
Yoon, Sungho [1 ]
机构：
[1] Chung Ang Univ, Dept Chem, Seoul 06974, South Korea
[2] Seoul Natl Univ, Dept Chem, Seoul 08826, South Korea
[3] Korea Inst Sci & Technol, Clean Energy Res Ctr, Seoul 136791, South Korea
来源：
INORGANIC CHEMISTRY | 2021年 / 60卷 / 10期
基金：
新加坡国家研究基金会;
关键词：
RUTHENIUM PINCER COMPLEX; POROUS ORGANIC POLYMER; SELECTIVE HYDROGENATION; HOMOGENEOUS HYDROGENATION; UNSATURATED ALDEHYDES; CYCLIC CARBONATES; ACTIVATED CARBON; SCALE SYNTHESIS; EFFICIENT; METHANOL;
D O I：
10.1021/acs.inorgchem.0c03681
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
In this study, a commercially available homogeneous pincer-type complex, Ru-Macho, was directly heterogenized via the Lewis acid-catalyzed Friedel-Crafts reaction using dichloromethane as the cross-linker to obtain a heterogeneous, pincer-type Ru porous organometallic polymer (Ru-Macho-POMP) with a high surface area. Notably, Ru-Macho-POMP was demonstrated to be an efficient heterogeneous catalyst for the chemoselective hydrogenation of alpha,beta-unsaturated carbonyl compounds to their corresponding allylic alcohols using cinnamaldehyde as a model compound. The Ru-Macho-POMP catalyst showed a high turnover frequency (TOF = 920 h(-1)) and a high turnover number (TON = 2750), with high chemoselectivity (99%) and recyclability during the selective hydrogenation of alpha, beta-unsaturated carbonyl compounds.
引用
收藏
页码：6881 / 6888
页数：8
相关论文
共 95 条
[1]   Study of Precatalyst Degradation Leading to the Discovery of a New Ru0 Precatalyst for Hydrogenation and Dehydrogenation [J].
Anaby, Aviel ;
Schelwies, Mathias ;
Schwaben, Jonas ;
Rominger, Frank ;
Hashmi, A. Stephen K. ;
Schaub, Thomas .
ORGANOMETALLICS, 2018, 37 (13) :2193-2201
[2]   Hydrogenation of citral on activated carbon and high-surface-area graphite-supported ruthenium catalysts modified with iron [J].
Bachiller-Baeza, B ;
Guerrero-Ruiz, A ;
Wang, P ;
Rodríguez-Ramos, I .
JOURNAL OF CATALYSIS, 2001, 204 (02) :450-459
[3]   Ru-PPh3@porous organic polymer: efficient and stable catalyst for the trickle bed regioselective hydrogenation of cinnamaldehyde [J].
Chen, Xingkun ;
Zhu, Hejun ;
Song, Xiangen ;
Du, Hong ;
Wang, Tao ;
Zhao, Ziang ;
Ding, Yunjie .
REACTION KINETICS MECHANISMS AND CATALYSIS, 2017, 120 (02) :637-649
[4]   Tuneable Hydrogenation of Nitriles into Imines or Amines with a Ruthenium Pincer Complex under Mild Conditions [J].
Choi, Jong-Hoo ;
Prechtl, Martin H. G. .
CHEMCATCHEM, 2015, 7 (06) :1023-1028
[5]   ZIRCONIA-SUPPORTED MONOMETALLIC RU AND BIMETALLIC RU-SN, RU-FE CATALYSTS - ROLE OF METAL-SUPPORT INTERACTION IN THE HYDROGENATION OF CINNAMALDEHYDE [J].
COQ, B ;
KUMBHAR, PS ;
MOREAU, C ;
MOREAU, P ;
FIGUERAS, F .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (40) :10180-10188
[6]   HYDROGENATION OF ALPHA, BETA-UNSATURATED CARBONYLS - ACROLEIN HYDROGENATION ON GROUP-VIII METAL-CATALYSTS [J].
COQ, B ;
FIGUERAS, F ;
GENESTE, P ;
MOREAU, C ;
MOREAU, P ;
WARAWDEKAR, M .
JOURNAL OF MOLECULAR CATALYSIS, 1993, 78 (02) :211-226
[7]   Water-enhanced selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on RuSnB/CeO2 catalysts [J].
Dai, Yihu ;
Chu, Xiaofang ;
Gu, Jingjing ;
Gao, Xing ;
Xu, Min ;
Lu, Di ;
Wan, Xiaoyue ;
Qi, Wei ;
Zhang, Bingsen ;
Yang, Yanhui .
APPLIED CATALYSIS A-GENERAL, 2019, 582
[8]   An efficient heterogeneous catalytic system for chemoselective hydrogenation of unsaturated ketones in aqueous medium [J].
Deshmukh, Amit ;
Kinage, Anil ;
Kumar, Rajiv ;
Meijboom, Reinout .
POLYHEDRON, 2010, 29 (17) :3262-3268
[9]   Chemoselective hydrogenation of cinnamaldehyde: A comparison of the immobilization of Ru-phosphine complex on graphite oxide and on graphitic surfaces [J].
Dongil, A. B. ;
Bachiller-Baeza, B. ;
Guerrero-Ruiz, A. ;
Rodriguez-Ramos, I. .
JOURNAL OF CATALYSIS, 2011, 282 (02) :299-309
[10]   Hydrogenation towards Synthetic Sandalwood Odorants in Fragrance Industry [J].
Dupau, Philippe .
HELVETICA CHIMICA ACTA, 2018, 101 (12)
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